𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Bossi (2026)

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Our top choices for Bossi hotels

A courtyard with stone walls, arched windows, and potted plants.

A swimming pool with a clear view of the surrounding landscape, including trees and distant hills.

A rustic interior with a stone wall, a wooden staircase, and a view of the outdoors.

An outdoor courtyard with stone walls, arched windows, and potted plants.

1. Castello di Bossi

Castelnuovo Berardenga

CESAR JAVIER

S$250

includes taxes & fees

24 Aug - 25 Aug

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

An interior corridor with arches, columns, and a brick wall.

2. La Certosa di Pontignano

Castelnuovo Berardenga

Edyta

S$111

includes taxes & fees

8 Sept - 9 Sept

A historic stone building with multiple windows and a courtyard.

An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.

A pool area with lounge chairs and a service person attending to a guest.

A stone building with outdoor seating and a garden with roses.

3. Borgo San Felice Resort

Castelnuovo Berardenga

Cynthia

S$1,018

includes taxes & fees

26 Aug - 27 Aug

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

A stone building with a wooden door, outdoor seating, and a pergola with vines.

A stone building with a window and a light fixture.

A pool surrounded by lush greenery and vineyards, with a stone building in the background.

4. Agriturismo San Sano

Gaiole in Chianti

Paula

S$196

includes taxes & fees

26 Aug - 27 Aug

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A stone building with a tower, surrounded by people dining at tables with candles.

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

A historic stone building with a large arched window and a small balcony.

5. Castello di Tornano Wine Resort

Gaiole in Chianti

Austin

S$315

includes taxes & fees

25 Aug - 26 Aug

A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

A table set for breakfast with various dishes, drinks, and a newspaper.

A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.

6. Hotel Le Fontanelle

Castelnuovo Berardenga

Malcolm

S$815

includes taxes & fees

2 Sept - 3 Sept

A terrace with multiple sun loungers and a scenic view of green fields and hills.

An indoor swimming pool with lounge chairs and a view of the countryside.

A spa room with a reception desk, a massage chair, and a window with blinds.

A modern hotel room with a bed, a small table with a hat, a red chair, a window with curtains, and a bathroom with a glass shower enclosure.

7. Precise House Montaperti Siena

Asciano

Dieter

S$173

includes taxes & fees

30 Aug - 31 Aug

A table set for dining with a scenic view of rolling hills and distant mountains.

A courtyard with brick buildings, a column, and potted plants.

An aerial view of a property with a swimming pool, surrounded by trees and a view of the countryside.

A brick building with a large arched entrance, a metal gate, and a wooden door.

8. Castello di Leonina Relais

Asciano

Meghan

S$198

includes taxes & fees

23 Aug - 24 Aug

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

9. Dievole Wine Resort

Castelnuovo Berardenga

Nicole

S$436

includes taxes & fees

26 Aug - 27 Aug

A modern building with a sign reading "Palace Hotel."

A modern building entrance with a glass door reflecting a parking lot and trees.

A red building with a reception sign, a bicycle, potted plants, and luggage.

10. Palace Hotel Due Ponti

Due Ponti

borjan

S$131

includes taxes & fees

22 Aug - 23 Aug

A spacious lobby with a modern white sofa set, a glass coffee table, and a large abstract painting on the wall.

A dining table set with wine glasses, a candle, and cutlery, with a view of greenery outside.

A hotel entrance with a sign reading "HOTEL EXPO".

A modern living room with a glass coffee table, white sofas, and decorative plants.

11. Hotel Executive

Scacciapensieri

Susan

S$134

includes taxes & fees

23 Aug - 24 Aug

A table set for breakfast with a scenic view of hills and a cloudy sky.

An open wooden door leading to a courtyard with potted plants and a view of buildings in the background.

A two-story building with a central entrance, green shutters, and a brick staircase leading up to the door.

An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

12. Palazzo di Valli

Siena

Payton

S$198

includes taxes & fees

26 Aug - 27 Aug

A modern hotel lobby with a high ceiling and a glass roof, featuring wooden paneling, comfortable seating, and a large wall mural.

A reception area with a wooden reception desk, two chairs, a vase with flowers, and a large pillar.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

13. Four Points by Sheraton Siena

Scacciapensieri

Raul

S$220

includes taxes & fees

1 Sept - 2 Sept

A narrow stone pathway leading to a rustic building with a wooden door and a window.

A cozy living room with a fireplace, wooden beams, and comfortable seating.

A cozy living room with a striped sofa, a wooden coffee table, and a bookshelf.

A well-lit outdoor garden area with stone planters, a paved walkway, and a building with large windows.

14. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Giancarlo

S$273

includes taxes & fees

25 Aug - 26 Aug

A large building with multiple rooms, surrounded by a field of lavender.

An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.

An arched brick corridor leading to a dining area with tables set for a meal.

A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.

15. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Qingwen

S$732

includes taxes & fees

26 Aug - 27 Aug

A hotel with a courtyard featuring sun loungers and a covered seating area.

A hotel room with a bed, a bedside table, and a window with curtains.

A room with a checkered floor, a patterned sofa, and a wall with framed portraits.

A buffet setup with various food items and a large framed menu on the wall.

16. Hotel Palazzo dei Priori

Siena

Kerry

S$129

includes taxes & fees

30 Aug - 31 Aug

A swimming pool with a clear blue water, surrounded by well-maintained grass and hedges.

A cozy dining area with a table set for two, a vase of dried flowers, and candles on the table.

A bathroom with a sink, mirror, and shower.

A hotel room with a bed, two bedside tables, a telephone, and wall-mounted light fixtures.

17. Sangallo Park Hotel

Vico Alto

Linda

S$154

includes taxes & fees

28 Aug - 29 Aug

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

A stone building with a garden, tall trees, and a clear blue sky.

A room with a large window offering a view of a hilly landscape. There is a sofa with patterned upholstery and a lamp on a side table.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

18. Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

Rama

S$537

includes taxes & fees

6 Sept - 7 Sept

A courtyard with a lemon tree, potted plants, and a building with arched windows.

A building with a symmetrical facade, a central staircase, and a gravel pathway leading to the entrance.

A room with a large window offering a view of a landscaped garden with trees and a pathway.

A large, historic building with a covered patio and a well-maintained garden.

19. Villa Scacciapensieri Boutique Hotel

Scacciapensieri

Nigel

S$325

includes taxes & fees

28 Aug - 29 Aug

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.

A spacious living area with a high arched ceiling, a sofa set, and a glass coffee table.

An indoor dining area with brick arches, tables set for dining, and a view of the outdoors.

20. The Club House

Castelnuovo Berardenga

Karla

S$1,125

includes taxes & fees

8 Sept - 9 Sept

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Top Bossi Hotel Reviews

Hotel Chiusarelli

8/10 Good

"The hotel itself was very nice. The staff were super helpful and we enjoyed our time. The AC and wifi were both a little weak, but otherwise, it was a pleasant stay. The breakfast buffet was also very good with a large selection."

Borgo Vescine

10/10 Excellent

"Had an amazing time. Rooms can be a bit hot at times but everything else was spectacular. Highly recommended"

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back"

Villa Casagrande Resort & SPA

10/10 Excellent

"A beautiful hotel in a lovely little town. The staff were amazing, so helpful. The rooms were very clean and comfortable. I didn’t use the indoor pool or spa facilities so can’t comment on them. The outdoor pool is across the road and up a steep hill, so great if you have a car but not so much if you are on foot! Overall a very good stay."

Hotel Athena

10/10 Excellent

"We had a superior room, which was very comfortable. We had dinner in the restaurant several times, and the food and drink was excellent. One evening we just enjoyed the cocktail bar, and the staff were fun! Breakfast buffet has everything one could want, and was always fresh. Free parking! You will have an uphill walk to the town centre, but no matter where you go in Siena it’s either up or down. Highly recommended."

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"

La Certosa di Pontignano

10/10 Excellent

"Great property with unique setting being an old monastery. We thought we had booked a room with A/C but there wasn’t. They moved us to a room with A/C at no additional cost."

Fattoria di Vegi

10/10 Excellent

"Amazing hotel! Looking forward to coming back."

More cheap stays in Bossi

Cannon d'Oro

Via Montanini 28 Siena SI

S$124

23 Aug - 24 Aug

includes taxes & fees

7.8/10 Good! (258 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

S$136

23 Aug - 24 Aug

includes taxes & fees

10/10 Exceptional! (48 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

S$145

23 Aug - 24 Aug

includes taxes & fees

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

S$146

23 Aug - 24 Aug

includes taxes & fees

8.8/10 Excellent! (104 reviews)

Castello di Bossi

Località Bossi Castelnuovo Berardenga SI

S$250

24 Aug - 25 Aug

includes taxes & fees

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

9.4/10 Exceptional! (23 reviews)

Frequently asked questions

Where is the best place to stay in Bossi?

Grand Hotel Continental Siena – Starhotels Collezione, located 7 mi (11.2 km) from the heart of Bossi, is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Hotel Athena and Borgo Scopeto Wine & Country Relais. See all available top hotels, or vacation rentals in Bossi.

What are some of the best holiday rentals that Bossi has to offer?

Borgo Argiano: This holiday home rental outside of Bossi is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an espresso maker. You can relax into your holiday with a garden and a library. See all vacation rentals in Bossi.

If I need to cancel my hotel reservation in Bossi, will I receive a refund?

Yes! Most hotel room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Bossi.

What's the best dog-friendly accommodation option in Bossi?

Castello di Bossi is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Bossi.

What are some accommodation options with pools in Bossi?

Borgo Scopeto Wine & Country Relais: Provides 2 restaurants, 2 outdoor swimming pools and a full-service spa. Castello di Leonina Relais and Castello di Spaltenna- Small Luxury Hotels of the World are a couple of other choices with an on-site pool. View all hotels with pools in Bossi.

What is staying in Bossi like?

Travellers to Bossi will find plenty to explore and enjoy. In Bossi, there are 20 hotels and other accommodation options to choose from. Find out more about Bossi.

What are the top places to visit in Bossi?

Places to visit in the wider area include Castle of Brolio, Siena Circuit and Cantalici Winery. You'll also find Meleto Castle and Terra di Seta in the area. Take a look at what more there is to see and do in Expedia's Bossi guide.

What's the seasonal weather like in Bossi?

The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Bossi is 946 mm.

Bossi Hotels from S$111

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Bossi

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Bossi hotels

1. Castello di Bossi

2. La Certosa di Pontignano

3. Borgo San Felice Resort

4. Agriturismo San Sano

5. Castello di Tornano Wine Resort

6. Hotel Le Fontanelle

7. Precise House Montaperti Siena

8. Castello di Leonina Relais

9. Dievole Wine Resort

10. Palace Hotel Due Ponti

11. Hotel Executive

12. Palazzo di Valli

13. Four Points by Sheraton Siena

14. Castello di Fonterutoli Wine Resort

15. Borgo Scopeto Wine & Country Relais

16. Hotel Palazzo dei Priori

17. Sangallo Park Hotel

18. Castello di Spaltenna- Small Luxury Hotels of the World

19. Villa Scacciapensieri Boutique Hotel

20. The Club House

Top Bossi Hotel Reviews

Hotel Chiusarelli

Borgo Vescine

Grand Hotel Continental Siena – Starhotels Collezione

Villa Casagrande Resort & SPA

Hotel Athena

Borgo Scopeto Wine & Country Relais

Castello di Spaltenna- Small Luxury Hotels of the World

La Certosa di Pontignano

Fattoria di Vegi

More cheap stays in Bossi

Cannon d'Oro

Torre del Fuggisole

Piccolo Hotel Etruria

Albergo Centrale

Castello di Bossi

Porta Pispini Residence

Frequently asked questions

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